I've been a fan of the Startup podcast since the first episode. In the last episode, "Fake It Til You Make It", Alex stated that the unfair advantage of Startup is the listening audience of the podcast. However, while that may be one unfair advantage, I don't think it's the key one.
The technology industry is grappling with it's incredible lack of diversity. Technology companies, both large and small, are overwhelmingly composed of White males. I think Gimlet's true unfair advantage is that it was founded by two White males. This in no way means that the two White males lack talent, drive, or hustle. However, I don't think that they would have persuaded investors to give them money if they had the same level of talent but came packaged as two Black males. Were any of the people you asked for money Black? Have the people who gave you money also invested in companies headed by Black founders? Have you interviewed any Black candidates for employment? Did you show your demo app to any Black people? I would hazard to guess that the answer to all of these questions is "no".
I think White maleness is the unfair advantage of Gimlet because you found other White males who gave you a chance. This may be, in part, because those investors saw themselves in you. However, that "pattern-matching" doesn't exist for Black startup founders. We usually have to be twice as good as the majority population in tech and execute flawlessly. White and Black startup founders may both be tightrope walkers, but the White side has a safety net. The Black side? Just ground and gravity.
The technology industry will continue to suffer from poor diversity unless young startup companies like Gimlet Media recognize the power of White privilege. The only way that diversity in tech can be improved is if this recognition translates into a willingness to make a change and use privilege as a vehicle for empowerment. That means seeking out diverse talent instead of the network of White people you're probably using to hire employees. I want Gimlet Media to be a great company, and I think that diversity is a key competitive advantage. Diverse companies create more innovative solutions and are better positioned to do business with the Browner America that we all see on the horizon.
I've thought a lot about the culture of Whiteness in technology. I even published a book in 2013 called "Minority Tech" (http://www.MinorityTech.com) about my own journey as a Black technologist. However, I am always aware that I could be wrong. If you think that Alex Blumberg could have built Gimlet if he was a Black man named Tyrone Jenkins, I would like to know how you think that would have been possible.